Acetic Acid → 2,2-Diacetoxyacetyl chloride

Participants

Reaction Steps

A mixture of glyoxylic acid monohydrate (53.2 g, 578 mmol), acetic anhydride (530 mL, 5.61 mol) and acetic acid (120 mL) was refluxed for 2 h, concentrated in vacuo and azeotroped with toluene. The residue was diluted with toluene, and thionyl chloride (84 mL, 1.15 mol) was added to the mixture. The resultant mixture was stirred at 60° C. for 16 h and concentrated in vacuo. The residue was purified by distillation (6-8 hpa, 70-80° C.) to afford compound the title compound as a colorless oil (70.7 g, 363 mmol, 63%).

Provenance & Evidence